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Fragrance precursors

Inactive Publication Date: 2005-09-06
GIVAUDAN SA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0013]Accordingly, it would be advantageous to have a fragrance delivery system which is capable of releasing a fragrant compound or compounds in a controlled manner, maintaining a desired smell over a prolonged period of time.
[0014]An object of the present invention is to provide fragrance precursors which are stable in an alkaline environment, especially in laundry products.
[0016]Also an object of the present invention is to provide fragrance precursors with high substantivity.
[0018]Also an object of the present invention is to provide fragrance precursors with slow release properties.

Problems solved by technology

There are, however, several drawbacks to this strategy.
The fragrance material can be too volatile and / or too soluble, resulting in fragrance loss during manufacturing, storage, and use.
Many fragrance materials are also unstable over time.
This again results in loss during storage.
However, these methods are often unsuccessful.
In addition, cyclodextrins can be too expensive.
Using this system in various consumer products leads to a prolonged perception of the fragrant compound(s) to be released.
This results in considerable loss of perfume and in particular the fruity notes.
Furthermore, they are water soluble and are, therefore, lost to some extent during the washing / rinsing cycle if introduced directly into detergents.
Therefore, these lactones are of limited use in laundry products, especially detergents.
However, it has not been described or suggested to use such phenacyl acetals as fragrance precursors, which are capable of releasing a fragrant ketone and a fragrant lactone over a prolonged period.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

example 1

Preparation of Cyclic Phenacyl Acetals

1. General Procedure for the Preparation of Hydroxy-acetophenones

[0124]A suspension of the corresponding bromo-acetophenone (0.05 mmol) and sodium formate (17 g, 0.25 mol, 5 eq.) in aqueous ethanol (85%, 150 ml) was heated at reflux until completion of the reaction (TLC). Most of the ethanol was evaporated and the mixture partitioned between MTBE (80 ml) and water (70 ml). The organic phase was separated and washed with aqueous NaHCO3 (sat.) and brine. Removal of the solvent in vacuo, after drying over MgSO4, afforded a crude product as a solid which was recrystallised from ethanol.

2-Hydroxy-1-(4-methoxy-phenyl)-ethanone

[0125]Obtained according to the general procedure.

[0126]mp 104-105° C. 1H-NMR (400 MHz, CDCl3): 3.48 (t, 1H, J 4); 4.82 (d, 2H, J 4); 6.95-7.0 (m, 2H); 7.85-7.95 (m, 2H). IR (νmax, cm−1, neat): 3415m, 2929w, 1672s, 1603s. MS [m / z (EI)]: 166 (M+, 4), 155 (100), 77 (28).

1-(3,5,5,6,8,8-Hexamethyl-5′,6′,7′,8′-tetrahydro-naphthalen-2-...

example 2

Photolysis of Cyclic Phenacyl Acetals (I) in Solutions

[0164]Photorelease assays were conducted on solutions (typical concentrations of precursors (I) were from 0.05% to 0.1% g / v) in organic solvents (preferably ethanol) or on cotton towels after deposition of the phenacyl acetals (I), as described below in the example 3.

[0165]The solutions were irradiated with a mercury lamp (150 W) in a borosilicate glass apparatus (PYREX®) so as to limit the irradiation window to mainly the UVA and UVB spectrum of sun light. The alcoholic solution was irradiated for one hour and samples taken every 15 min to analyze the extent of the photolysis.

Analysis

[0166]The presence of the aryl ketone (II) and lactone (III) after photolysis in solutions was determined by using GC retention times. Samples (0.2 μl) were injected (on column injection) without further dilution. Gas chromatography-flame ionization detection (GC-FID) was carried out with a Fisons-GC 8000series apparatus, using a J&W Scientific DB-5...

example 3

Spray Tests

[0169]1 g of an approximately 0.2% cyclic phenacyl acetal (I) solution in ethanol was evenly sprayed on a Terry towel (white cotton towel, 25cm×25 cm, 45 g), corresponding to 45-75 μg / g cotton. The sprayed towels were allowed to dry in a dark and odorless place. When dry, the towels were irradiated for a few seconds up to a few minutes with a tanning lamp (Osram ULTRA-VITALUX®, 300 W; at a distance of 50 cm, the light has approximately six to seven times the effect of the natural sunlight at noon on a sea-side mid-summer day). The evaluation was done by a trained panel of perfumers before and after irradiation. Before irradiation, the towels were judged to be odorless. The results after irradiation are summarized in table 2.

[0170]

TABLE 2Release of aryl ketones and lactones from cyclicphenacyl acetals on fabric upon irradiation with a tanninglamp.Fragrance Target(perception)*Globalaryl ketoneappre-STRUCTURE(II)lactone (III)ciation*1FIXOLIDE ® (++)METHYL LAITONE ® (+)+2FIXO...

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Abstract

The present invention provides a fragrance precursor of formula I: that is capable of forming a fragrant ketone of formula II: and a fragrant lactone of formula III:

Description

FIELD OF THE INVENTION[0001]The present invention relates to fragrance precursors for a fragrant ketone and a fragrant lactone.BACKGROUND OF THE INVENTION[0002]A principal strategy currently employed in imparting odors to consumer products is the admixing of the fragrance directly into the product. There are, however, several drawbacks to this strategy. The fragrance material can be too volatile and / or too soluble, resulting in fragrance loss during manufacturing, storage, and use. Many fragrance materials are also unstable over time. This again results in loss during storage.[0003]In many consumer products it is desirable for the fragrance to be released slowly over time. Micro-encapsulation and inclusion complexes with cyclodextrins have been used to help decrease volatility, improve stability and provide slow-release properties. However, these methods are often unsuccessful. In addition, cyclodextrins can be too expensive.[0004]Precursors for the delivery of organoleptic compound...

Claims

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Application Information

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IPC IPC(8): A61K8/49A61K8/30A61Q13/00C07D307/94C07D307/20C07D309/10C07D309/00C07D307/00C11B9/00C11D3/50C07D309/12
CPCA61K8/4973A61K8/498A61Q13/00C07D307/20C07D307/94C07D309/10C11B9/0034C11B9/0076C11D3/507A61K2800/57
Inventor GAUTSCHI, MARKUSPLESSIS, CAROLINEDERRER, SAMUEL
Owner GIVAUDAN SA
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